US2664400A - Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same - Google Patents
Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same Download PDFInfo
- Publication number
- US2664400A US2664400A US110236A US11023649A US2664400A US 2664400 A US2664400 A US 2664400A US 110236 A US110236 A US 110236A US 11023649 A US11023649 A US 11023649A US 2664400 A US2664400 A US 2664400A
- Authority
- US
- United States
- Prior art keywords
- reaction
- soyamine
- reaction product
- acid pyrophosphate
- reaction products
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000007795 chemical reaction product Substances 0.000 title claims description 25
- 239000002253 acid Substances 0.000 title claims description 9
- 239000000314 lubricant Substances 0.000 title claims description 9
- 235000011180 diphosphates Nutrition 0.000 title description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 11
- -1 FERROUS METALS Chemical class 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- 239000010687 lubricating oil Substances 0.000 description 6
- 239000013535 sea water Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 150000003139 primary aliphatic amines Chemical class 0.000 description 3
- 229940048084 pyrophosphate Drugs 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GOLAKLHPPDDLST-AVQMFFATSA-N (9e,12e)-octadeca-9,12-dien-1-amine Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCN GOLAKLHPPDDLST-AVQMFFATSA-N 0.000 description 1
- QGLWBTPVKHMVHM-MDZDMXLPSA-N (e)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C\CCCCCCCCN QGLWBTPVKHMVHM-MDZDMXLPSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/098—Esters of polyphosphoric acids or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
Definitions
- This invention relates to reaction products of an octyl acid pyrophosphate and a soyamine and lubricants containing the same.
- This reaction product when added in small amounts to lubricating oils has been found capable of protecting metal surfaces from rust even under severe conditions of use.
- soyamine and dioctyl acid pyrophosphate will give excellent protection against rusting of ferrous metals in both ordinary water and sea water, even when the reaction product is present in relatively low concentrations in the lubricant.
- the soyamine used in preparing the reaction product of this invention may be considered as a mixture of primary aliphatic amines prepared from soybean oil by subjecting the latter to hydrolysis and converting the carboxylater groups of the resulting fatty acids to amino groups.
- the latter may be accomplished, for example, by neutralizing the acids with ammonia, dehydrating the ammonium carboxylates to form the corresponding nitriles, and finally reducing the nitriles to amines.
- soyamines generally contain about 85 to 98% of primary aliphatic amines of 16 to 18 or more carbon atoms with about 80% of the amine content being in the form of unsaturated compounds such as octadecenyl and octadecadienyl primary amines. At least 70% of the preferred soyamine consists oi unsaturated aliphatic primary amines having at least 18 carbon atoms in the chain.
- a typical commercial soyamine known as Armeen SD (Distilled) contained 97% of primary amines 01" which was hexadecyl amine, 35% was octadecenyl amine, and 45% was octadecadienyl amine.
- soyamines of the above type may be reacted in various proportions with dioctyl acid pyrophosphate to form an oil-soluble reaction product which has utility as a rust inhibitor in lubricants and as intermediates in the production of other organic phosphorus containing products.
- the reaction is exothermic and it is preferred to control the reaction so as to avoid temperatures which might cause decomposition.
- a temperature of about 50 to 80 C. is quite satisfactory, though somewhat tures may be employed.
- Reaction products in gen to phosphorus are less than 1 are not as satwith ratios of 1 to 2.5 moles of soyamine per atom of phosphorus.
- Efcampl'e 1.'-'-Io 183.5 grams of distilled soyamine (97% primary amine) having an average molecular weightof 296 was slowly added 125 grams of dioctyl acid pyrophosphate while maintaining a temperature of about C. exothermic reaction had ceased the mixture was stirredforapproximately one hour to insure completion of the reaction.
- the product was quite efiective at 0.025% concentration in solvent-refined lubricating oil, in preventing the corrosion of steel in sea water.
- Example 3 The procedure of Example 1 was employed to make a reaction product from dioctyl acid pyrophosphate and a crude soyamine containing approximately 85% of primary aliphatic amines about of which were long chain unsaturated aliphatic amines. The proportions employed corresponded to a nitrogen to phosphorus ratio of approximately 1.1 to 1 (or a mol ratio of amine to pyrophosphate of 2.2 to 1). The product was similar to that of Example 1 and substantially as eifective as a corrosion inhibitor in lubricating oils.
- Example 4Dioctyl acid pyrophosphate was reacted with a soyamine having the approximate composition: 20% hexadecylamine, 50% 9-octadecenylamine, and 30% 9,12-octadecadienylamine to form a clear very viscous, pale amber material with a specific gravity of about 0.95.
- the reaction product had a molar ratio of nitrogen to phosphorus of about 1.0 and a pH of about 3 5.
- This product was tested in a solvent-refined lubricating oil for its ability to protect metal surfaces from the rusting action of sea water. The reaction product was added to each of several samples of the same oil with a different concentration in each.
- reaction products of the first three examples passed the resulting test with but few failures at the 0.025% concentration in the case of Examples 2 and 3. All samples of Examples 1 to 4 passed the rusting test at 0.05 concentration.
- the preferred dioctyl acid pyrcphosphate is the one having the Z-ethylhexyl isomer as each octyl group.
- Lubricants conta'ning reaction products of an alkyl acid phosphate and soyamine are disclosed and claimed in our copending application Serial No. 110,237, filed August 13, 1949.
- reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least 70% of unsaturated aliphatic primary amines each having at least 18 carbon atoms in 4 the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.
- a lubricant for ferrous metals comprising a hydrocarbon oil and a rust-inhibiting quantity of an oil-soluble reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least of unsaturated aliphatic primary amines each having at least 18 carbon atoms in the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Description
Patented Dec. 29, 1953 UNITE pc'rs or AN, PYROPHOSPHATE AND so A I E .AND LUBRICANTS CONTAINING THE SAME REACTION PRO ocTiZL non) Willard H. Woodstock, Crete, and Thomas M.
Beck, Homewood,
assignors to Victor Chemical Works, a corporation of Illinois No Drawing. ApplicationAugust 13, 19.49, Serial No. 110,236
Claims. (01. 252- -32 :5)
This invention relates to reaction products of an octyl acid pyrophosphate and a soyamine and lubricants containing the same. This reaction product when added in small amounts to lubricating oils has been found capable of protecting metal surfaces from rust even under severe conditions of use.
An number of oil additives have in the past as rust inhibitors, but been satisfactory for use in lubricating oils where severe corrosion conditions are encountered such as arepresent where the lubricated surfaces come in contact with sea water.
been proposed these have not We have found that the reaction product of.
soyamine and dioctyl acid pyrophosphate will give excellent protection against rusting of ferrous metals in both ordinary water and sea water, even when the reaction product is present in relatively low concentrations in the lubricant. v
The soyamine used in preparing the reaction product of this invention may be considered as a mixture of primary aliphatic amines prepared from soybean oil by subjecting the latter to hydrolysis and converting the carboxylater groups of the resulting fatty acids to amino groups. The latter may be accomplished, for example, by neutralizing the acids with ammonia, dehydrating the ammonium carboxylates to form the corresponding nitriles, and finally reducing the nitriles to amines. Commercially obtainable soyamines generally contain about 85 to 98% of primary aliphatic amines of 16 to 18 or more carbon atoms with about 80% of the amine content being in the form of unsaturated compounds such as octadecenyl and octadecadienyl primary amines. At least 70% of the preferred soyamine consists oi unsaturated aliphatic primary amines having at least 18 carbon atoms in the chain. A typical commercial soyamine known as Armeen SD (Distilled) contained 97% of primary amines 01" which was hexadecyl amine, 35% was octadecenyl amine, and 45% was octadecadienyl amine.
We have found that soyamines of the above type may be reacted in various proportions with dioctyl acid pyrophosphate to form an oil-soluble reaction product which has utility as a rust inhibitor in lubricants and as intermediates in the production of other organic phosphorus containing products. The reaction is exothermic and it is preferred to control the reaction so as to avoid temperatures which might cause decomposition. A temperature of about 50 to 80 C. is quite satisfactory, though somewhat tures may be employed.
higher temperacontaining acids as impurities.
Reaction products in gen to phosphorus are less than 1 are not as satwith ratios of 1 to 2.5 moles of soyamine per atom of phosphorus. 'A reaction product having 'a ratio within "the rangeof 1 to 1.1 "is generally preferred. Suitable reaction products were made in accordance with the following examples,
Efcampl'e 1.'-'-Io 183.5 grams of distilled soyamine (97% primary amine) having an average molecular weightof 296 was slowly added 125 grams of dioctyl acid pyrophosphate while maintaining a temperature of about C. exothermic reaction had ceased the mixture was stirredforapproximately one hour to insure completion of the reaction. was a low melting oil-soluble solid and represents the addition reaction productof 2 moles of soyamine-and 1 mole of dioctyl acid pyrophosphate. The product was quite efiective at 0.025% concentration in solvent-refined lubricating oil, in preventing the corrosion of steel in sea water.
eating grade hydrocarbon oils and was quite efiective as a corrosion inhibitor in such oils at concentrations as low as 0.05%.
Example 3.The procedure of Example 1 was employed to make a reaction product from dioctyl acid pyrophosphate and a crude soyamine containing approximately 85% of primary aliphatic amines about of which were long chain unsaturated aliphatic amines. The proportions employed corresponded to a nitrogen to phosphorus ratio of approximately 1.1 to 1 (or a mol ratio of amine to pyrophosphate of 2.2 to 1). The product was similar to that of Example 1 and substantially as eifective as a corrosion inhibitor in lubricating oils.
Example 4.Dioctyl acid pyrophosphate was reacted with a soyamine having the approximate composition: 20% hexadecylamine, 50% 9-octadecenylamine, and 30% 9,12-octadecadienylamine to form a clear very viscous, pale amber material with a specific gravity of about 0.95. The reaction product had a molar ratio of nitrogen to phosphorus of about 1.0 and a pH of about 3 5. This product was tested in a solvent-refined lubricating oil for its ability to protect metal surfaces from the rusting action of sea water. The reaction product was added to each of several samples of the same oil with a different concentration in each. Each of these samples was subdivided into four test portions and tested according to A. S. T. M. method D-665-42T, but using, in place of the distilled water specified therein a synthetic sea water prepared according to Procedure B of A. S. T. M. method D665'-47T.
All four portions of each of the four oil samples containing respectively 0.025, 0.05, 0.1 and 0.2% by weight of the reaction product passed the test. A sample of the same oil containing no additive failed to pass the test.
When tested in a manner similar to the above, the reaction products of the first three examples passed the resulting test with but few failures at the 0.025% concentration in the case of Examples 2 and 3. All samples of Examples 1 to 4 passed the rusting test at 0.05 concentration.
When using soyamine as the sole additive to the lubricating oil, the resulting tests failed at all of the concentrations mentioned above.
The preferred dioctyl acid pyrcphosphate is the one having the Z-ethylhexyl isomer as each octyl group.
Lubricants conta'ning reaction products of an alkyl acid phosphate and soyamine are disclosed and claimed in our copending application Serial No. 110,237, filed August 13, 1949.
Having disclosed our invention in considerable detail, it is our intention that the invention be not limited by any of the details of description unless otherwise specified, but rather be construed broadly within its spirit and scope as set out in the accompanying claims.
We claim:
1. The reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least 70% of unsaturated aliphatic primary amines each having at least 18 carbon atoms in 4 the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.
2. The reaction product of claim 1 wherein said ester is the substantially pure dioctyl acid pyrophosphate.
3. The reaction product of claim 1 wherein the proportions are approximately one mole of amine per one atom of phosphorus.
4. A lubricant for ferrous metals comprising a hydrocarbon oil and a rust-inhibiting quantity of an oil-soluble reaction product prepared by reacting a dioctyl acid ester of pyrophosphoric acid with 1 to 2.5 moles, per atom of phosphorus in the ester, of an amine composition containing at least of unsaturated aliphatic primary amines each having at least 18 carbon atoms in the molecule until the reaction is substantially completed, the reaction being carried out at a temperature below that at which substantial decomposition of the reaction product occurs.
5. The lubricant of claim 4 wherein the ester of said reaction product is the substantially pure dioctyl acid pyrophosphate.
WILLARD H. WOCDSTOCK. THOMAS M. BECK.
References Cited in the file of this patent OTHER REFERENCES Gerrard, J. Chem. Soc. (London), pages 1464 to 1469 (1940). (Copy available in Scientific Library.)
Claims (1)
- 4. A LUBRICANT FOR FERROUS METALS COMPRISING OF HYDROCARBON OIL AND A RUST-INHIBITING QUANTITY OF AN OIL-SOLUBLE REACTION PRODUCT PREPARED BY REACTING A DIOCTYL ACID ESTER OF PYROPHOSPHORIC ACID WITH 1 TO 2.5 MOLES, PER ATOM OF PHOSPHORUS IN THE ESTER, OF AN AMINE COMPOSITION CONTAINING AT LEAST 70% OF UNSATURATED ALIPHATIC PRIMARY AMINES EACH HAVING AT LEAST 18 CARBON ATOMS IN THE MOLECULE UNTIL THE REACTION IS SUBSTANTIALLY COMPLETED, THE REACTION BEING CARRIED OUT AT A TEMPERATURE BELOW THAT AT WHICH SUBSTANTIAL DECOMPOSITION OF THE REACTION PRODUCT OCCURS.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US110236A US2664400A (en) | 1949-08-13 | 1949-08-13 | Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US110236A US2664400A (en) | 1949-08-13 | 1949-08-13 | Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same |
Publications (1)
Publication Number | Publication Date |
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US2664400A true US2664400A (en) | 1953-12-29 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US110236A Expired - Lifetime US2664400A (en) | 1949-08-13 | 1949-08-13 | Reaction products of an octyl acid pyrophosphate and soyamine and lubricants containing the same |
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Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2841126A (en) * | 1955-05-09 | 1958-07-01 | Gulf Oil Corp | Marine diesel fuel compositions and methods of operating marine diesel engines |
US2848414A (en) * | 1955-11-23 | 1958-08-19 | Universal Oil Prod Co | Corrosion inhibitor |
US2863904A (en) * | 1955-05-09 | 1958-12-09 | Gulf Oil Corp | Amine salts of di oxo-octyl orthophosphates |
US2961408A (en) * | 1957-06-14 | 1960-11-22 | Shell Oil Co | Power transmission mineral oil base fluids |
US3000820A (en) * | 1959-04-15 | 1961-09-19 | Standard Oil Co | Thixotropic oleaginous compositions containing the reaction product of an abietyl amine and an organic phosphate |
US3051655A (en) * | 1957-11-01 | 1962-08-28 | Quaker Chemical Products Corp | Metalworking lubricant |
US3150039A (en) * | 1960-11-16 | 1964-09-22 | Union Carbide Corp | Insecticidal method using both pyrophosphoric and polyphosphoric acid partial ester ammonium salts and process for preparing same |
US3504055A (en) * | 1967-10-06 | 1970-03-31 | Mobil Oil Corp | Neutral primary tertiaralkyl amine salts of tripolyphosphoric acid and phosphoric acid alkyl esters |
US3652242A (en) * | 1970-02-02 | 1972-03-28 | Mobil Oil Corp | Liquid hydrocarbon fuels containing alkylamine salts |
WO2018200664A1 (en) * | 2017-04-27 | 2018-11-01 | The Lubrizol Corporation | Method of lubricating a mechanical device with high pyrophosphate level lubricant |
WO2019204141A1 (en) * | 2018-04-18 | 2019-10-24 | The Lubrizol Corporation | Lubricant with high pyrophosphate level |
US11352582B2 (en) | 2015-11-06 | 2022-06-07 | The Lubrizol Corporation | Lubricant with high pyrophosphate level |
US11384308B2 (en) | 2016-07-20 | 2022-07-12 | The Lubrizol Corporation | Alkyl phosphate amine salts for use in lubricants |
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US2005619A (en) * | 1934-11-10 | 1935-06-18 | Du Pont | Esters of acids of phosphorus |
US2080299A (en) * | 1935-04-12 | 1937-05-11 | Du Pont | Inhibiting corrosion of metals |
US2285854A (en) * | 1934-02-23 | 1942-06-09 | Du Pont | Lubrication |
US2371655A (en) * | 1941-12-06 | 1945-03-20 | Gulf Oil Corp | Lubricant compositions |
US2371854A (en) * | 1943-09-27 | 1945-03-20 | Gulf Oil Corp | Mineral oil composition |
US2397381A (en) * | 1943-03-19 | 1946-03-26 | Gulf Oil Corp | Mineral oil compositions and methods of suppressing foaming in oils |
US2400611A (en) * | 1945-03-19 | 1946-05-21 | Gulf Oil Corp | Turbine oils |
US2413852A (en) * | 1944-08-30 | 1947-01-07 | Atlantie Refining Company | Rust-inhibiting lubricant |
-
1949
- 1949-08-13 US US110236A patent/US2664400A/en not_active Expired - Lifetime
Patent Citations (8)
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US2285854A (en) * | 1934-02-23 | 1942-06-09 | Du Pont | Lubrication |
US2005619A (en) * | 1934-11-10 | 1935-06-18 | Du Pont | Esters of acids of phosphorus |
US2080299A (en) * | 1935-04-12 | 1937-05-11 | Du Pont | Inhibiting corrosion of metals |
US2371655A (en) * | 1941-12-06 | 1945-03-20 | Gulf Oil Corp | Lubricant compositions |
US2397381A (en) * | 1943-03-19 | 1946-03-26 | Gulf Oil Corp | Mineral oil compositions and methods of suppressing foaming in oils |
US2371854A (en) * | 1943-09-27 | 1945-03-20 | Gulf Oil Corp | Mineral oil composition |
US2413852A (en) * | 1944-08-30 | 1947-01-07 | Atlantie Refining Company | Rust-inhibiting lubricant |
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Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2841126A (en) * | 1955-05-09 | 1958-07-01 | Gulf Oil Corp | Marine diesel fuel compositions and methods of operating marine diesel engines |
US2863904A (en) * | 1955-05-09 | 1958-12-09 | Gulf Oil Corp | Amine salts of di oxo-octyl orthophosphates |
US2848414A (en) * | 1955-11-23 | 1958-08-19 | Universal Oil Prod Co | Corrosion inhibitor |
US2961408A (en) * | 1957-06-14 | 1960-11-22 | Shell Oil Co | Power transmission mineral oil base fluids |
US3051655A (en) * | 1957-11-01 | 1962-08-28 | Quaker Chemical Products Corp | Metalworking lubricant |
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US11352582B2 (en) | 2015-11-06 | 2022-06-07 | The Lubrizol Corporation | Lubricant with high pyrophosphate level |
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WO2018200664A1 (en) * | 2017-04-27 | 2018-11-01 | The Lubrizol Corporation | Method of lubricating a mechanical device with high pyrophosphate level lubricant |
CN110573599A (en) * | 2017-04-27 | 2019-12-13 | 路博润公司 | Method for lubricating a mechanical device with a lubricant having a high pyrophosphate content |
US11180710B2 (en) | 2017-04-27 | 2021-11-23 | The Lubrizol Corporation | Method of lubricating a mechanical device with high pyrophosphate level lubricant |
CN110573599B (en) * | 2017-04-27 | 2022-04-26 | 路博润公司 | Method for lubricating a mechanical device with a lubricant having a high pyrophosphate content |
WO2019204141A1 (en) * | 2018-04-18 | 2019-10-24 | The Lubrizol Corporation | Lubricant with high pyrophosphate level |
CN112055743A (en) * | 2018-04-18 | 2020-12-08 | 路博润公司 | Lubricant with high pyrophosphate content |
CN112055743B (en) * | 2018-04-18 | 2022-11-04 | 路博润公司 | Lubricant with high pyrophosphate content |
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